Triethylamine → HCID 19827485, compound
Reaction equation
[OH:1][C:2]([C:8]1[CH:9]=[N:10][CH:11]=[N:12][CH:13]=1)([CH:5]([CH3:7])[CH3:6])[C:3]#[CH:4].I[C:15]1[S:16][CH:17]=[CH:18][CH:19]=1.C(N(CC)CC)C.CCCCCC.C(OCC)(=O)C>C(#N)C>[OH:1][C:2]([C:8]1[CH:13]=[N:12][CH:11]=[N:10][CH:9]=1)([CH:5]([CH3:7])[CH3:6])[C:3]#[C:4][C:15]1[S:16][CH:17]=[CH:18][CH:19]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 65 °C
Procedure
3-Hydroxy-4-methyl-3-pyrimidin-5-ylpent-1-yne (1 g, 5.7 mmol), prepared as in Stage (2), 2-iodothiophene (1.2 g, 5.7 mmol), triethylamine (2 ml, 14.5 mmol), copper-I-iodide (mg), and bis(triphenylphosphine)palladium-II-chloride (200 mg) were brought together in dry acetonitrile (55 ml) and the mixture was heated at 65° C. under nitrogen. After 1 hour, the mixture was cooled, quenched in dilute aqueous HCl, neutralised with dilute aqueous ammonia and extracted with ether (3×15 ml). The combined organic extracts were washed with dilute aqueous ammonia, water, and brine before being dried over magnesium sulphate and concentrated under reduced pressure to give an oil. Flash chromatography on silica eluting with hexane-ethyl acetate (1:3) gave the title compound as a solid of melting point 113°-14.5° C.
Workup
- temperaturethe mixture was cooled
- customquenched in dilute aqueous HCl
- extractionextracted with ether (3×15 ml)
- washThe combined organic extracts were washed with dilute aqueous ammonia, water, and brine
- dry with materialbefore being dried over magnesium sulphate
- concentrationconcentrated under reduced pressure
- customto give an oil
Sources & evidence
- ORD record
- ord-e56371dbe358421f98803ed84a4750aa
- Source dataset
- uspto-grants-1991_06
- Patent number
- US05026418
Reaction notes
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